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The amide group of the title compound, C7H5Cl2NO, forms a dihedral angle of 76.64 (5)° with the plane of the benzene ring. In the crystal structure, inter­molecular N—H...Cl and N—H...O hydrogen bonds link mol­ecules, forming one-dimensional chains in the c-axis direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806005289/lh6591sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806005289/lh6591Isup2.hkl
Contains datablock I

CCDC reference: 295948

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.030
  • wR factor = 0.078
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

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Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2,6-dichlorobenzamide top
Crystal data top
C7H5Cl2NODx = 1.524 Mg m3
Mr = 190.02Melting point: 196 K
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 17745 reflections
a = 12.7941 (9) Åθ = 3.5–25.8°
b = 13.5868 (8) ŵ = 0.72 mm1
c = 9.5283 (6) ÅT = 173 K
V = 1656.31 (18) Å3Needle, colorless
Z = 80.42 × 0.20 × 0.20 mm
F(000) = 768
Data collection top
Stoe IPDS-II two-circle
diffractometer
1556 independent reflections
Radiation source: fine-focus sealed tube1486 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ω scansθmax = 25.6°, θmin = 3.7°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1515
Tmin = 0.752, Tmax = 0.869k = 1613
16372 measured reflectionsl = 1111
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.0334P)2 + 0.9959P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
1556 reflectionsΔρmax = 0.30 e Å3
109 parametersΔρmin = 0.38 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0098 (13)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.66990 (3)0.47318 (4)0.64618 (5)0.04017 (18)
Cl20.84012 (4)0.74376 (4)0.29460 (6)0.0488 (2)
N10.88652 (12)0.50808 (11)0.38477 (15)0.0299 (3)
H1A0.8503 (17)0.4998 (18)0.304 (3)0.044 (6)*
H1B0.9486 (19)0.4821 (16)0.387 (2)0.040 (6)*
O10.90267 (8)0.57900 (8)0.59937 (11)0.0256 (3)
C10.74694 (11)0.61229 (10)0.46944 (14)0.0198 (3)
C20.65837 (11)0.57668 (12)0.53862 (16)0.0232 (3)
C30.56070 (13)0.62076 (13)0.52519 (17)0.0320 (4)
H30.50190.59490.57370.038*
C40.55038 (14)0.70310 (14)0.43974 (19)0.0366 (4)
H40.48400.73370.42970.044*
C50.63597 (16)0.74096 (12)0.3691 (2)0.0356 (4)
H50.62860.79720.31070.043*
C60.73298 (13)0.69567 (12)0.38470 (16)0.0274 (4)
C70.85294 (11)0.56459 (11)0.48903 (15)0.0200 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0313 (3)0.0482 (3)0.0410 (3)0.01246 (18)0.01176 (18)0.0246 (2)
Cl20.0492 (3)0.0509 (3)0.0464 (3)0.0158 (2)0.0061 (2)0.0268 (2)
N10.0265 (7)0.0407 (8)0.0226 (7)0.0103 (6)0.0081 (6)0.0109 (6)
O10.0245 (6)0.0339 (6)0.0184 (5)0.0043 (4)0.0062 (4)0.0034 (5)
C10.0250 (7)0.0199 (7)0.0145 (6)0.0011 (6)0.0065 (6)0.0030 (5)
C20.0255 (8)0.0267 (8)0.0174 (7)0.0004 (6)0.0070 (6)0.0002 (6)
C30.0240 (8)0.0446 (10)0.0275 (8)0.0028 (7)0.0056 (7)0.0068 (7)
C40.0327 (9)0.0386 (10)0.0384 (9)0.0155 (8)0.0140 (8)0.0105 (8)
C50.0486 (11)0.0225 (8)0.0358 (10)0.0094 (7)0.0188 (8)0.0010 (7)
C60.0355 (9)0.0226 (8)0.0242 (7)0.0016 (6)0.0081 (7)0.0026 (6)
C70.0221 (7)0.0202 (7)0.0178 (7)0.0016 (5)0.0024 (5)0.0016 (6)
Geometric parameters (Å, º) top
Cl1—C21.7463 (16)C1—C71.515 (2)
Cl2—C61.7444 (18)C2—C31.392 (2)
N1—C71.327 (2)C3—C41.390 (3)
N1—H1A0.91 (2)C3—H30.9500
N1—H1B0.87 (2)C4—C51.384 (3)
O1—C71.2444 (18)C4—H40.9500
C1—C21.397 (2)C5—C61.393 (2)
C1—C61.403 (2)C5—H50.9500
C7—N1—H1A122.8 (14)C5—C4—C3120.58 (15)
C7—N1—H1B120.7 (14)C5—C4—H4119.7
H1A—N1—H1B116 (2)C3—C4—H4119.7
C2—C1—C6116.61 (14)C4—C5—C6119.25 (16)
C2—C1—C7121.32 (13)C4—C5—H5120.4
C6—C1—C7122.04 (14)C6—C5—H5120.4
C3—C2—C1122.40 (15)C5—C6—C1122.11 (16)
C3—C2—Cl1118.45 (13)C5—C6—Cl2118.82 (13)
C1—C2—Cl1119.16 (11)C1—C6—Cl2119.07 (13)
C4—C3—C2119.05 (16)O1—C7—N1123.92 (14)
C4—C3—H3120.5O1—C7—C1119.64 (13)
C2—C3—H3120.5N1—C7—C1116.44 (13)
C6—C1—C2—C30.1 (2)C4—C5—C6—Cl2179.74 (13)
C7—C1—C2—C3178.30 (14)C2—C1—C6—C50.3 (2)
C6—C1—C2—Cl1179.90 (11)C7—C1—C6—C5178.51 (14)
C7—C1—C2—Cl11.66 (19)C2—C1—C6—Cl2179.72 (11)
C1—C2—C3—C40.1 (2)C7—C1—C6—Cl22.06 (19)
Cl1—C2—C3—C4179.90 (12)C2—C1—C7—O175.45 (19)
C2—C3—C4—C50.1 (2)C6—C1—C7—O1102.70 (17)
C3—C4—C5—C60.1 (3)C2—C1—C7—N1103.92 (17)
C4—C5—C6—C10.3 (2)C6—C1—C7—N177.94 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl1i0.91 (2)2.78 (2)3.5936 (15)150.4 (18)
N1—H1A···O1i0.91 (2)2.32 (2)2.9728 (18)128.5 (18)
N1—H1B···O1ii0.87 (2)2.08 (2)2.9491 (18)178 (2)
Symmetry codes: (i) x, y+1, z1/2; (ii) x+2, y+1, z+1.
 

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